Holiday rentals in Chesapeake Bay
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Top-rated holiday rentals in Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Chesapeake Bay holiday rentals
Other great holiday rentals in Chesapeake Bay
Guest favourite
Farm stay in Madison
4.98 out of 5 average rating, 166 reviewsMadison Nature Getaway
Guest favourite
Farm stay in Cardinal
4.91 out of 5 average rating, 117 reviewsWtrfrnt aptmnt w/pool/dock on private farm
Guest favourite
Cottage in Onancock
4.97 out of 5 average rating, 203 reviewsEscape to the Eastern Shore - Upscale w dock
Guest favourite
Farm stay in Cape Charles
5.0 out of 5 average rating, 337 reviewsPrivate Guesthouse on Secluded Waterfront Farm
Guest favourite
Tiny home in Machipongo
4.98 out of 5 average rating, 267 reviewsMachipongo Glamper
Guest favourite
Home in Reedville
4.98 out of 5 average rating, 124 reviewsSunkissed Cottage-private, natural waterfront home
Guest favourite
Flat in Lexington Park
4.97 out of 5 average rating, 515 reviewsHistoric St. Mary's City, MD
Guest favourite
Home in Chestertown
5.0 out of 5 average rating, 40 reviewsWaterfront house with private dock & kayaks!
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